Chemical composition and QSAR descriptor of the dichloromethane extract of Moringa olifera (L.) flowers
Messaouda Allaoui*1, Oumelkheir Rahim2, Djamila Hamada3, Manel Zaoui-Djelloul Daouadji4, Brahim LABED5
1VPRS Laboratory, Chemistry Department, Faculty of Mathematic and Matter Sciences.
University of Kasdi Merbah, Ouargla 30000, Algeria.
2Pollution and Waste Treatment Laboratory, Chemistry Department, Faculty of Mathematics and Matter Sciences, University Kasdi Merbah, Ouargla 30000, Algeria.
3Process Engineering Laboratory, Applied Sciences Faculty,
University of Kasdi Merbah, Ouargla 30000, Algeria.
4VPRS Laboratory, Chemistry Department, Faculty of Mathematic and Matter Sciences.
University of KASDI Merbah, Ouargla 30000, Algeria.
5Superior Normal School, Ouargla, Algeria
*Corresponding Author E-mail: aamessaouda@gmail.com
ABSTRACT:
The Moringa oleifera (Moringaceae) is one of these important plants, distributed in many tropical and sub-tropical countries, known with its medical uses of high nutritional value it is called the "tree of life". The Composition profile of the dichloromethane extract of the flowers of Moringa oleifera growing in Algerian desert was studied by capillary gas chromatography-mass spectrometry (GC-MS). thirty four Compounds were identified; Within the limits of the applied experimental conditions and by interpreting the mass spectra obtained and comparing it with the mass spectra of the reference materials, we record the possibility of the presence of the following chemical compounds: Hydrocarbons, Organic acids, Esters, Aldehydes Aromatic compounds and Nitrocyclic compounds, which major compounds are : (Z) - (9,17Octadecadienal (100%), Octadecanoic acid (60.4%), Heneicosane (10.186%), (Z)-9 Octadecenoic acid (12.711%), Heptadecanoic acid (13.742%), Hexadecane, 2,6,10,14-tetramethyl (18.988%), Heptadecane (14.866%) and Eicosane (17.535%). Analysis of QSAR descriptor from the results revealed that major constituents of the dichloromethane extract of Moringa olifera (L.) flowers.
World Health Organisation (WHO) has estimated that 4 billion people (80% of the world population) use herbal medicines for some aspect of primary health care3.
The Moringaceae is a monotype family of sole genus Moringa with 10 to 12 species in tropical world. Moringa trees are an important food commodity as almost all plant parts are edible and consumed as nutritive vegetable in many countries4. Moringa oleifera is one of these important plants, distributed in many tropical and sub-tropical countries, known with its medical uses of high nutritional value. This plant has been used by ancient Romans, Greeks, and Egyptians. In Indian ethnotherapeutic system of medicine, M. oleifera is reported to possess hypoglycemic activity. Since it is a significant source of fats, proteins, beta-carotene, vitamin C, iron, potassium, and other nutrients, The WHO has recommended to Moringa as an alternative to imported food supplies for the treatment of malnutrition. Besides being edible5. all parts of the M. oleifera have long been deployed for the treatment of numberless diseases such as: a treatment for anemia, loss of appetite and increases lactation in women - the pain gastric, stomach ulcer, diarrhea, dysentery, colitis and it can be used as a laxative, purgative and diuretic-colds, bronchitis, fever and headache - rheumatism, cramps muscle bruises and bruises - skin infections, scabies, yeast infections, insect bites. Moringa can also be used in some cases of diabetes to stabilize blood sugar levels and can stabilize6-8. Such leaf of Moringa oleifera (ML) have been proven to have: antioxidant9-14, anti-inflammatory15,16, anticancer17,18, anti-hypertensive19, hypolipidemic20, hypoglycemic21,22, antimicrobial23-25 and hepatoprotective18,26. Several research works have reported the use of chromatographic analytical study (GC/MS) of the various parts of Moringa oleifera from various regions of the world which reconfirmed the presence of several bioactive compounds: esters, alcohols, aldehydes, ketones, acids, furans and lactones, nitrogen-compounds, sulfur-compounds, hydrocarbons and pyrans27-33.
This paper presents qualitative identification of the content of volatiles compounds present in the flowers of Moringa oleifera growing in Algerian desert by using of gaz chromatography coupled with mass spectrometry.
MATERIALS AND METHODS:
Plant material:
The flowers of Moringa oleifera were collected in December 2016 from Tamanrasset (Province in southern Algeria). The plant is identified by Pr. Chahma Abdelmadjid and dried under shade before being grounded.
Extraction:
50 g of the flowers of Moringa oleifera were macerated four times for 24 hours with 70% EtOH solution. The hydro-alcoholic solutions were concentrated under reduced pressure and the residue was dissolved in water and kept in a cold place overnight. After filtration, the aqueous solution was successively extracted with CH2Cl2, EtOAc and n-BuOH for three times for each solvent, then the extracts were concentrated.
The residues obtained by CH2Cl2 were dissolved in hexane and subjected to GC/MS analysis.
Gas Chromatography-Mass Spectrometry:
The dichloromethane extracts were dissolved in hexane and injected into a GC-MS apparatus (Hewlett Packard Model 5890 series) equipped with a mass selective detector (mass HP 5972). Experimental conditions for capillary GC-MS analysis were developed under the following conditions: Capillary column HP5-MS, 30 m x 0.32 mm, total flow 1.9mL/min, injector temperature 250 °C, injection mode Splitless, temperature 45-270°C, detector temperature 300°C
QSAR’s descriptor study:
Structure activity Relationships-Using QSAR properties of HyperChem software, we explored the biological properties of eight derives of the results revealed that major constituents of the dichloromethane extract (table 1) taken from GC-MS analyses with their descriptors as Molecular weight (MW), Molecular volume (MV), Molecular surface (MS), the octanol/water partition coefficient (LogP), polarizability, refractivity, hydratation energy, are the properties studied in the present work.
RESULT:
Fig 1: Chromatogram obtained from the GC-MS with the extract of Moringa oleifera flowers.Table 1: Constituents of the dichloromethane extract of Moringa olifera (L.) flowers.
|
N° |
Retention Time (min) |
Compound Name |
Chemical Structure |
Peak Area (%) |
Ratio (%) |
Qual |
|
1 |
28.27 |
Spiro[2.4]heptane, 4-methylene |
|
0.647 |
2.623 |
58 |
|
2 |
28.58 |
Phenol, 2,6-bis(1,1-dimethylethyl)-4- |
|
2.395 |
9.703 |
98 |
|
3 |
29.23 |
d-Nerolidol |
|
1.265 |
5.124 |
91 |
|
4 |
29.47 |
Dodecanoic acid |
|
0.326 |
1.320 |
91 |
|
5 |
31.43 |
Tetradecanoic acid |
|
1.46 |
5.914 |
98 |
|
6 |
31.76 |
1,3-Benzenediol, 5-methyl- |
|
1.077 |
4.365 |
83 |
|
7 |
32.23 |
1-Tetradecanol |
|
1.063 |
4.307 |
94 |
|
8 |
32.56 |
Methyl 9-Methylundecanoate |
|
0.452 |
1.833 |
64 |
|
9 |
32.87 |
Hexadecanoic acid |
|
1.201 |
4.686 |
97 |
|
10 |
33.11 |
Octadecanoic acid |
|
14.967 |
60.640 |
95 |
|
11 |
33.67 |
9-Octadecenoic acid (Z)- |
|
0.692 |
2.804 |
93 |
|
12 |
33.80 |
Pentadecanoic acid |
|
1.167 |
4.729 |
91 |
|
13 |
34.04 |
Ether, 1-hexadecenyl methyl |
|
0.952 |
3.858 |
53 |
|
14 |
34.38 |
9,17-Octadecadienal, (Z)- |
|
24.681 |
100.000 |
98 |
|
15 |
35.10 |
9-Octadecenal |
|
0.645 |
2.614 |
49 |
|
16 |
35.24 |
Heneicosane |
|
2.514 |
10.186 |
91 |
|
17 |
35.68 |
9-Octadecenoic acid (Z)- |
|
3.137 |
12.711 |
93 |
|
18 |
35.83 |
Heptadecanoic acid |
|
3.392 |
13.742 |
93 |
|
19 |
36.51 |
Octadecane, 1-chloro- |
|
1.650 |
6.687 |
38 |
|
20 |
36.68 |
Hexadecane, 2,6,10,14-tetramethyl- |
2,6,10,14-tetramethyl-Hexadecane
|
4.687 |
18.988 |
95 |
|
21 |
37.167 |
1,2-Benzenedicarboxylic acid, 3-nitro |
|
1.775 |
7.191 |
72 |
|
22 |
37.47 |
1-Hexadecene |
|
1.739 |
7.045 |
53 |
|
23 |
38.23 |
1-Dotriacontanol |
|
1.386 |
5.617 |
95 |
|
24 |
38.33 |
Nonadecane |
|
0.604 |
2.448 |
83 |
|
25 |
38.51 |
Heptadecane |
|
3.669 |
14.866 |
96 |
|
26 |
38.69 |
Hexadecadienoic acid, methyl ester |
This name appears to be ambiguous |
1.178 |
4.775 |
89 |
|
27 |
38.82 |
1,2-Epoxy-1-vinylcyclododecene |
Caution: Valence appears to be exceeded |
1.198 |
4.854 |
74 |
|
28 |
39.15 |
9,12-Octadecadienoyl chloride, (Z,Z) |
|
0.550 |
2.227 |
95 |
|
29 |
39.64 |
Hexatriacontane |
|
1.301 |
5.273 |
50 |
|
30 |
40.16 |
11-Methylsqualene |
|
0.782 |
3.167 |
59 |
|
31 |
40.78 |
17-Pentatriacontene |
|
1.366 |
5.536 |
91 |
|
32 |
41.21 |
Eicosane |
|
4.328 |
17.535 |
94 |
|
33 |
41.64 |
Pyridinium, 1-hexadecyl-, chloride |
|
0.310 |
1.254 |
62 |
|
34 |
44.55 |
Thiazolo[5,4-d]pyrimidine, 7-methyl- |
|
0.975 |
3.949 |
50 |
Results are listed respectively in Fig 1. and Table 1 Showed GC-MS analysis led to the identification of number of compounds of the dichloromethane flowers extract of Moringa oleifera. Thirty-four Compounds were identified; Within the limits of the applied experimental conditions and by interpreting the mass spectra obtained and comparing it with the WILEY138 library, which are listed with their retention time (RT), molecular formula and area % in Table 1. Which major compounds are: (Z) - (9,17Octadecadienal (100%), Octadecanoic acid (60.4%), Heneicosane (10.186%), (Z)-9 Octadecenoic acid (12.711%), Heptadecanoic acid (13.742%), Hexadecane, 2,6,10,14-tetramethyl (18.988%), Heptadecane (14.866%) and Eicosane (17.535%). It has been reported that most of these compounds possess important activity such as: antibacterial, antifungal, antioxidant and anti-inflammatory 34-38.
QSAR’s descriptor study:
Table 2: Geometric optimization, all analyses and chemical proprieties for structure of major molecule of the extract, by HyperChem 8.0.6 software
|
N° |
All analyse
|
Stricture 3D |
Chemical proprieties |
|
10 |
stearic acid (Octadecanoic acid) Chemical Formula: C18H36O2 Exact Mass: 284.27 Molecular Weight: 284.48 m/z: 284.27 (100.0%), 285.27 (19.5%), 286.28 (1.8%) Elemental Analysis: C, 76.00; H, 12.76; O, 11.25 |
|
Boiling Point: 756.95 [K] Melting Point: 452.72 [K] Critical Temp: 809.65 [K] Critical Pres: 12.25 [Bar] Critical Vol: 1067.5 [cm3/mol] Gibbs Energy: -243.23 [kJ/mol] Henry's Law: 2.98 Heat of Form: -765.12 [kJ/mol] tPSA: 37.3 CLogP: 8.27 CMR: 8.7146 LogS: -5.006 pKa: 4.702 |
|
14 |
(Z)-octadeca-9,17-dienal((Z)- 9,17-Octadecadienal ) Chemical Formula: C18H32O Exact Mass: 264.25 Molecular Weight: 264.45 m/z: 264.25 (100.0%), 265.25 (19.5%), 266.25 (1.8%) Elemental Analysis: C, 81.75; H, 12.20; O, 6.05 |
|
Boiling Point: 660.94 [K] Melting Point: 327.28 [K] Critical Temp: 775.74 [K] Critical Pres: 12.96 [Bar] Critical Vol: 1021.5 [cm3/mol] Gibbs Energy: 169.22 [kJ/mol] Henry's Law: 0.77 Heat of Form: -257.78 [kJ/mol] tPSA: 17.07 CLogP: 7.272 CMR: 8.5107 LogS: -4.966 |
|
16 |
Henicosane(Heneicosane) Chemical Formula: C21H44 Exact Mass: 296.34 Molecular Weight: 296.58 m/z: 296.34 (100.0%), 297.35 (22.7%), 298.35 (2.5%) Elemental Analysis: C, 85.05; H, 14.95 |
|
Boiling Point: 680.08 [K] Melting Point: 325.93 [K] Critical Temp: 766.57 [K] Critical Pres: 9.56 [Bar] Critical Vol: 1211.5 [cm3/mol] Gibbs Energy: 125.94 [kJ/mol] Henry's Law: -3.69 Heat of Form: -476.77 [kJ/mol] tPSA: 0 CLogP: 11.803 CMR: 9.9172 LogS: -7.3 |
|
17 |
oleic acid((Z)-9-Octadecenoic acid) Chemical Formula: C18H34O2 Exact Mass: 282.26 Molecular Weight: 282.47 m/z: 282.26 (100.0%), 283.26 (19.5%), 284.26 (1.8%) Elemental Analysis: C, 76.54; H, 12.13; O, 11.33 |
|
Boiling Point: 761.11 [K] Melting Point: 447.64 [K] Critical Temp: 816.32 [K] Critical Pres: 12.71 [Bar] Critical Vol: 1047.5 [cm3/mol] Gibbs Energy: -163.01 [kJ/mol] Henry's Law: 2.74 Heat of Form: -647.9 [kJ/mol] tPSA: 37.3 CLogP: 7.786 CMR: 8.6892 LogS: -4.754 pKa: 4.699 |
|
18 |
Heptadecanoic acid heptadecanoic acid Chemical Formula: C17H34O2 Exact Mass: 270.26 Molecular Weight: 270.46 m/z: 270.26 (100.0%), 271.26 (18.4%), 272.26 (1.6%) Elemental Analysis: C, 75.50; H, 12.67; O, 11.83 |
|
Boiling Point: 734.07 [K] Melting Point: 441.45 [K] Critical Temp: 798.91 [K] Critical Pres: 13.12 [Bar] Critical Vol: 1011.5 [cm3/mol] Gibbs Energy: -251.65 [kJ/mol] Henry's Law: 2.8 Heat of Form: -744.48 [kJ/mol] tPSA: 37.3 CLogP: 7.741 CMR: 8.2508 LogS: -4.743 pKa: 4.702 |
|
20 |
(Hexadecane, 2,6,10,14-tetramethyl-) 2,6,10,14-tetramethylhexadecane Chemical Formula: C20H42 Exact Mass: 282.33 Molecular Weight: 282.56 m/z: 282.33 (100.0%), 283.33 (21.6%), 284.34 (2.2%) Elemental Analysis: C, 85.02; H, 14.98 |
|
Boiling Point: 655.44 [K] Melting Point: 254.66 [K] Critical Temp: 721.59 [K] Critical Pres: 10.37 [Bar] Critical Vol: 1131.5 [cm3/mol] Gibbs Energy: 107.76 [kJ/mol] Henry's Law: -3.57 Heat of Form: -477.25 [kJ/mol] tPSA: 0 CLogP: 10.754 CMR: 9.4534 LogS: -6.972 |
|
25 |
heptadecane Chemical Formula: C17H36 Exact Mass: 240.28 Molecular Weight: 240.48 m/z: 240.28 (100.0%), 241.29 (18.4%), 242.29 (1.6%) Elemental Analysis: C, 84.91; H, 15.09 |
|
Boiling Point: 588.56 [K] Melting Point: 280.85 [K] Critical Temp: 718.4 [K] Critical Pres: 12.31 [Bar] Critical Vol: 987.5 [cm3/mol] Gibbs Energy: 92.26 [kJ/mol] Henry's Law: -3.2 Heat of Form: -394.21 [kJ/mol] tPSA: 0 CLogP: 9.687 CMR: 8.062 LogS: -5.946 |
|
32 |
icosane Chemical Formula: C20H42 Exact Mass: 282.33 Molecular Weight: 282.56 m/z: 282.33 (100.0%), 283.33 (21.6%), 284.34 (2.2%) Elemental Analysis: C, 85.02; H, 14.98 |
|
Boiling Point: 657.2 [K] Melting Point: 314.66 [K] Critical Temp: 755.37 [K] Critical Pres: 10.16 [Bar] Critical Vol: 1155.5 [cm3/mol] Gibbs Energy: 117.52 [kJ/mol] Henry's Law: -3.57 Heat of Form: -456.13 [kJ/mol] tPSA: 0 CLogP: 11.274 CMR: 9.4534 LogS: -7.037 pKa: N/A |
All the calculations of structures of the major constituent’s derivatives were performed using HyperChem 8.0.6 software. The QSAR descriptors were compound molecular weight (amu), molecular surface (Ų), molecular volume (ų), LogP, polarizability (ų), refractivity (ų) hydratation Energy (Kcal/mol)
Table (3) summarize the QSAR’S properties of the major constituted of CH2Cl2 extract.
|
Compounds |
E min (Stability energy) |
MW (amu) |
POL (ų) |
MR (ų) |
Log P |
HE (Kcal/mol) |
MV |
SAG (Ų) |
|
Kcal/mol |
(ų) |
|||||||
|
10 |
12.177 |
283.475 |
34.072 |
82.956 |
10.629 |
5.917 |
1108.792 |
685.626 |
|
14 |
15.234 |
264.451 |
33.506 |
86.521 |
5.815 |
16.87 |
1066.007 |
660.663 |
|
16 |
13.023 |
296.58 |
39.309 |
98.423 |
8.826 |
9.124 |
1253.979 |
770.81 |
|
17 |
13.959 |
281.459 |
33.88 |
84.073 |
10.369 |
4.785 |
1096.368 |
678.504 |
|
18 |
11.541 |
269.448 |
32.237 |
78.355 |
10.233 |
5.543 |
1054.527 |
655.778 |
|
20 |
19.749 |
282.553 |
37.474 |
93.613 |
8.167 |
7.183 |
1144.199 |
683.789 |
|
25 |
10.479 |
240.473 |
31.969 |
80.019 |
7.241 |
7.633 |
1036.024 |
645.761 |
|
32 |
12.387 |
282.553 |
37.474 |
93.822 |
8.43 |
8.751 |
1199.386 |
739.144 |
CONCLUSION:
In the light of the results obtained, it was found thirty-four Compounds in the dichloromethane flowers extract of Moringa oleifera, most of these compounds possess important activity such as: antibacterial, antifungal, antioxidant and anti-inflammatory,which major compounds are: (Z) - (9,17Octadecadienal (100%), Octadecanoic acid (60.4%), Heneicosane (10.186%), (Z)-9 Octadecenoic acid (12.711%), Heptadecanoic acid (13.742%), Hexadecane, 2,6,10,14-tetramethyl (18.988%), Heptadecane (14.866%) and Eicosane (17.535%).
ACKNOWLEDGEMENTS:
The authors would like to thank the Algerian Ministry of Higher Education and Scientific Research for their support and providing the necessary facilities to carry out this research
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Received on 08.08.2022 Modified on 13.09.2022
Accepted on 01.10.2022 ©AJRC All right reserved
Asian J. Research Chem. 2022; 15(6):409-416.